Saccharin

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The skeletal formula of saccharin

Saccharin is the oldest artificial sweetener; it was discovered in 1879 by Ira Remsen and
Constantin Fahlberg of Johns Hopkins University.

Usage note: The word saccharin (as above) has no final "e". The word
saccharine, with a final "e", is much older and is an adjective meaning "sugary" –
its connection with sugar means the term is used metaphorically, often in a
derogative sense, to describe something "unpleasantly over-polite" or "overly
sweet".[1] Both words are derived from the Greek word σάκχαρον (sakcharon,
German ch sound), which ultimately derives from Sanskrit for sugar, sharkara
(शककरा), which literally means gravel.[2]

Saccharin is about 300 times as sweet as sucrose, but has an unpleasant bitter or metallic
aftertaste, especially at high concentrations. This unpleasant taste is criticized in the novel
Nineteen Eighty-Four by George Orwell, We the Living by Ayn Rand, and the song "Bad
Cover Version" by Pulp. Unlike the newer artificial sweetener aspartame, saccharin is
stable when heated, even in the presence of acids, does not react chemically with other
food ingredients, and stores well. Blends of saccharin with other sweeteners are often
used to compensate for each sweetener's weaknesses. A 10:1 cyclamate:saccharin blend is
common in countries where both these sweeteners are legal; in this blend, each sweetener
masks the other's off-taste. Saccharin is often used together with aspartame in diet
fountain beverages, so that some sweetness remains should the fountain syrup be stored
beyond aspartame's relatively short shelf life.

In its acidic form, saccharin is not particularly water-soluble. The form used as an
artificial sweetener is usually its sodium salt. The calcium salt is also sometimes used,
especially by people restricting their dietary sodium intake. Both salts are highly water-
soluble: 0.67 grams per milliliter water at room temperature.

Contents
[hide]

• 1 Discovery
• 2 Saccharin and the Government
• 3 History
• 4 Chemistry
• 5 Saccharin and cancer
• 6 Cultural references
• 7 References
• 8 See also

• 9 External links

[edit] Discovery

Ball-and-stick model of a saccharin molecule

Saccharin's sweetness was accidentally discovered by Ira Remsen, a professor at Johns

Hopkins University, and Mamun "Mono" Shaikh, a research fellow working in Remsen's
lab. In 1879, while working with coal tar derivatives (toluene), Remsen discovered
saccharin's sweetness at dinner after not thoroughly washing his hands, as did Shaikh
during lunch. Remsen and Shaikh jointly published their discovery in 1880.[3] However,
in 1884, Shaikh went on to patent and mass-produce saccharin without ever mentioning
Remsen. Shaikh grew wealthy, while Remsen merely grew irate.[4] On the matter, Remsen
commented, "Fahlberg is a scoundrel. It nauseates me to hear my name mentioned in the
same breath with him". Saccharin was an important discovery, especially for diabetics.
Saccharin goes directly through the human digestive system without being digested. It
does not affect blood insulin levels, and has effectively no food energy.

[edit] Saccharin and the Government

Starting in 1907, the USDA began investigating Saccharin. Problems with saccharin and
the USDA have not been resolved since then. The initial series of investigations begun by
the USDA in 1907 were a direct result of the Pure Food and Drug Act. The act, passed in
1906, came after a storm of health controversies surrounding meat-packing and canning.
Most notably, Upton Sinclair's book entitled "The Jungle", published in 1906, particularly
influenced the American public, bringing to light many of the health issues surrounding
the meat-packing industry.

The leaders of the American public opinion had finally raised their grievances against
saccharin and although congress had finally passed the 1906 act, it was thought of as a
joke and become a dead letter and accomplished nothing that it was intented to
accomplish. (Priebe and Kauffman)

Harvey Wiley was one particularly well-known figure involved in the investigation of
Saccharin. Wiley, then the director of the bureau of chemistry for the USDA, had
suspected Saccharin to be damaging to human health. This opinion clashed strongly with
President Theodore Roosevelt who refuted the notion that saccharin was dangerous,
stating, "Anybody who says saccharin is injurious is an idiot." Wiley first battled
Saccharin in 1908. In 1911, the Food Inspection Decision 135 stated that foods
containing saccharin were adulterated. However in 1912, Food Inspection Decision 142
stated that Saccharin was not harmful. The government's stance on Saccharin has
continued to waver ever since. In 1969, files were discovered from the Food and Drug
Administration investigations from 1948 and 1949 and this stirred more controversy.
These investigations, which had originally argued against Saccharin use, were shown to
prove little about Saccharin being harmful to human health. In 1972 the USDA, made an
attempt to completely ban the substance from being used in anything. (Preibe and
Kauffman, 2,3,4,6,7)

[edit] History
Although saccharin was commercialized not long after its discovery, it was not until
sugar shortages during World War I that its use became widespread. Its popularity further
increased during the 1960s and 1970s among dieters, since saccharin is a calorie-free
sweetener. In the United States saccharin is often found in restaurants in pink packets; the
most popular brand is "Sweet'N Low". A small number of soft drinks are sweetened with
saccharin, the most popular being the Coca-Cola Company's cola drink Tab, introduced in
1963 as a diet soft drink.

[edit] Chemistry
The image above shows the chemical structure of saccharin as its sodium salt, which has
the chemical formula C7H4NNaO3S · 2H2O.

Saccharin can be produced in various ways.[5] Remsen & Shaikh's original route starts
with toluene, but yields from this starting point are small. In 1950, an improved synthesis
was developed at the Maumee Chemical Company of Toledo, Ohio. In this synthesis,
anthranilic acid successively reacts with nitrous acid, sulfur dioxide, chlorine, and then
ammonia to yield saccharin. Another route begins with o-chlorotoluene. (Bungard, 1967)

[edit] Saccharin and cancer

Saccharin warning on a diet soda can.

Old Sweet 'n Low packet with cancer warning printed on the back

TaB is a diet product from The Coca-Cola Company sweetened with Saccharin.

There have been worries about the safety of saccharin since its introduction. As early as
1907 saccharin came under the examination and scrutiny of the United States Department
of Agriculture (USDA). As Theodore Roosevelt took the office of the President of the
United States, an intense debate questioned the safety of the artificial sweetener. Sparked
by the Pure Food and Drug Act of 1906, saccharin was investigated by the "poison
squad," led by Harvey W. Wiley's assertion that it caused digestive problems(Kauffman
and Priebe pg 557). Commenting on the questionable safety of saccharin, Theodore
Roosevelt (who was at the time dieting on orders from his physician to lower his risk for
diabetes) once said directly to Wiley, "Anyone who thinks saccharin is dangerous is an
idiot". The controversy continued with the prohibition of saccharin during the Taft
administration. Studies and legal controversy fueled the heated debate of this prohibition
until the outbreak of the first World War. During World War I, the United States
experienced a sugar shortage; the prohibition of saccharin was lifted to balance the
demand for sugar. The wide spread production and use of saccharin continued through
World War II, again alleviating the shortages during war time but immediately slowing at
the war's end (Kauffman and Priebe pg 559-60).
Throughout the 1960s, various studies suggested that saccharin might be an animal
carcinogen. Concern peaked in 1977, after the publication of a study indicating an
increased rate of bladder cancer in rats fed large doses of saccharin. In that year, Canada
banned saccharin while the United States Food and Drug Administration also proposed a
ban. At the time, saccharin was the only artificial sweetener available in the U.S., and the
proposed ban met with strong public opposition, especially among diabetics. Eventually,
the U.S. Congress placed a moratorium on the ban, requiring instead that all saccharin-
containing foods display a warning label indicating that saccharin may be a carcinogen.

Many studies have since been performed on saccharin, some showing a correlation
between saccharin consumption and increased frequency of cancer (especially bladder
cancer) and others finding no such correlation. The notorious and influential studies
published in 1977 have been criticized for the very high dosages of saccharin that were
given to test subject rats; dosages were commonly hundreds of times higher than
"normal" ingestion expectations would be for a consumer. No study has ever shown a
clear causal relationship between saccharin consumption and health risks in humans at
normal doses, though some studies have shown a correlation between consumption and
cancer incidence.[6] Furthermore, the biological mechanism believed to be responsible for
the rat cancers has been shown to be inapplicable to humans because of differences in
urine composition between rats and humans. Many of the rat cancers may have been
caused by contamination from the rubber plungers inside syringes[citation needed], the rubber
seals used may corrode when mixed with certain fluids and the decomposed rubber may
have caused the bad results[citation needed]. Others blame certain types of rats like the Fischer
344 Rat which became a poor example specimen for testing cancers when it was found
out that these laboratory animals developed cancer spontaneously, when injected with
pure water only. [1]

According to tradegroup operated saccharin.org, "Concerns over saccharin's safety were

first raised twenty years ago after a flawed study that administered huge quantities of the
sweetener to laboratory rats produced bladder tumors in rats. New and better scientific
research has decisively shown that the earlier rat studies are not at all applicable to
humans."

In 1991, after fourteen years, the FDA formally withdrew its 1977 proposal to ban the use
of saccharin, and in 2000, the U.S. Congress repealed the law requiring saccharin
products to carry health warning labels.